کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
9954079 | 1537673 | 2018 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Plant hydroperoxide-cleaving enzymes (CYP74 family) function as hemiacetal synthases: Structural proof of hemiacetals by NMR spectroscopy
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کلمات کلیدی
HMBCTMSHPLtrimethylsilylEASHSQCHASTOCSYDES - ازAOS - بهDivinyl ether synthase - دی دیینیل اتر سنتازEpoxyalcohol synthase - سنتاز اپوکسی الکلAllene oxide synthase - سنتاز اکسید آلنCytochrome P450 - سیتوکروم پی۴۵۰Heteronuclear single quantum coherence spectroscopy - طیف سنجی تک هسته ای تک هسته ای کوانتومیTotal correlation spectroscopy - طیف سنجی مجموع همبستگیcorrelation spectroscopy - طیف سنجی همبستگیheteronuclear multiple-bond correlation spectroscopy - طیف سنجی همبستگی چند باند هترونیکی هسته ایMethyl - متیلHydroperoxide isomerase - هیدروپراکسید ایزومرازHydroperoxide lyase - هیدروپراکسید لیازCOSY - کثیف
موضوعات مرتبط
علوم زیستی و بیوفناوری
بیوشیمی، ژنتیک و زیست شناسی مولکولی
زیست شیمی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Hydroperoxide lyases (HPLs) of the CYP74 family (P450 superfamily) are widely distributed enzymes in higher plants and are responsible for the stress-initiated accumulation of short-chain aldehydes. Fatty acid hydroperoxides serve as substrates for HPLs; however, details of the HPL-promoted conversion are still incompletely understood. In the present work, we report first time the micropreparative isolation and the NMR structural studies of fatty acid hemiacetal (TMS/TMS), the short-lived HPL product. With this aim, linoleic acid 9(S)âhydroperoxide (9(S)âHPOD) was incubated with recombinant melon hydroperoxide lyase (CmHPL, CYP74C2) in a biphasic system of water/hexane for 60â¯s at 0â¯Â°C, pHâ¯4.0. The hexane layer was immediately decanted and vortexed with a trimethylsilylating mixture. Analysis by GC-MS revealed a major product, i.e. the bis-TMS derivative of a hemiacetal which was conclusively identified as 9âhydroxyâ9â[(1â²E,3â²Z)ânonadienyloxy]ânonanoic acid by NMR-spectroscopy. Further support for the hemiacetal structure was provided by detailed NMR-spectroscopic analysis of the bis-TMS hemiacetal generated from [13C18]9(S)âHPOD in the presence of CmHPL. The results obtained provide incontrovertible evidence that the true products of the HPL group of enzymes are hemiacetals, and that the short-chain aldehydes are produced by their rapid secondary chain breakdown. Therefore, we suggest replacing the name “hydroperoxide lyase”, which does not reflect the factual isomerase (intramolecular oxidoreductase) activity, with “hemiacetal synthase” (HAS).
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids - Volume 1863, Issue 10, October 2018, Pages 1316-1322
Journal: Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids - Volume 1863, Issue 10, October 2018, Pages 1316-1322
نویسندگان
Lucia S. Mukhtarova, Fredi Brühlmann, Mats Hamberg, Bulat I. Khairutdinov, Alexander N. Grechkin,